Skip to content
2000
  1. Home
  2. A-Z Publications
  3. Current Pharmaceutical Design
  4. Volume 31, Issue 13
  5. Article
Volume 31, Issue 13
  • ISSN: 1381-6128
  • E-ISSN: 1873-4286

Abstract

Introduction

An efficient and four-component one-pot facile synthesis of tetra-substituted imidazole is achieved by cyclo-condensation reaction of benzil with subsequent successive substitution of aromatic aldehydes, ester substituted amine and ammonium acetate refluxing the mixture for almost two hours at 140°C.

Methods

The ending point of the understudy reaction was examined by TLC after regular intervals. Synthesized 1,2,4-tetrasubstituted imidazoles were characterized by physical data and the structural features were analyzed using spectroscopic techniques such as FTIR, NMR and elemental analysis.

Results

The inhibition potential of fabricated compounds was evaluated against the mushroom based Tyrosinase (polyphenol oxidase) enzyme. Tetra-substituted imidazole derivatives demonstrated significant potent tyrosinase inhibition activities.

Conclusion

Pharmacokinetic mechanism and molecular docking studies were also carried out.

© 2025 Bentham Science Publishers
Loading

Article metrics loading...

/content/journals/cpd/10.2174/0113816128330769241113095033
2025-01-02
2025-03-30

  • From This Site

    /content/journals/cpd/10.2174/0113816128330769241113095033
    dcterms_title,dcterms_subject,pub_keyword
    -contentType:Contributor -contentType:Concept -contentType:Institution
    10
    5
Loading full text...

Full text loading...

References

  1. SiwachA. VermaP.K. Synthesis and therapeutic potential of imidazole containing compounds.BMC Chem.20211511210.1186/s13065‑020‑00730‑1 33602331
     [Google Scholar]
  2. GaybullayevnaS.G. Heterocyclic compounds that are important in medicine.J Edu Devel Anal202224209213
     [Google Scholar]
  3. ShahzadK. AbbasF. PandeyD. AjmalS. KhadimM. TahirM.U. Synthesis, characterization and biological evaluation of novel tetrasubsituted imidazole compounds.ChemRxiv202010.26434/chemrxiv.12480605
     [Google Scholar]
  4. NarasimhanB. SharmaD. KumarP. Biological importance of imidazole nucleus in the new millennium.Med. Chem. Res.20112081119114010.1007/s00044‑010‑9472‑5
     [Google Scholar]
  5. LiuY. CaiL. LunJ. ZhaoM. GuoX. Enantiomeric separation and molecular docking study of seven imidazole antifungal drugs on a cellulose tris-(3,5-dimethylphenylcarbamate) chiral stationary phase.New J. Chem.20204442183371834610.1039/D0NJ03657A
     [Google Scholar]
  6. dos Santos NascimentoM.V.P. Mattar MunhozA.C. De Campos FacchinB.M. New pre-clinical evidence of anti-inflammatory effect and safety of a substituted fluorophenyl imidazole.Biomed. Pharmacother.20191111399140710.1016/j.biopha.2019.01.052 30841455
     [Google Scholar]
  7. NirwanN. PareekC. ChohadiaA.K. VermaK.K. Synthesis, antibacterial, and antifungal activities of 3-(4,5-Diphenyl-1H-imidazol-2-yl)-1H-Indole derivatives.J Sci Res202315115917010.3329/jsr.v15i1.59004
     [Google Scholar]
  8. NayakP. ChandrashekharK.S. PaiV. KamathV. MuddukrishnaB.S. PaiA. In silico design, synthesis, and antibacterial evaluation of novel triphenyl-substituted imidazoles.Rasayan J. Chem.20222022Special Issue111810.31788/RJC.2022.1558061
     [Google Scholar]
  9. El-ShahatM. El-SofanyW.I. SolimanA.G.A. HasaninM. Newly synthesized imidazolotriazole, imidazolotriazine, and imidazole-pyrazole hybrid derivatives as promising antimicrobial agents.J. Mol. Struct.2022125013172710.1016/j.molstruc.2021.131727
     [Google Scholar]
  10. NikitinaP.A. BasanovaE.I. NikolaenkovaE.B. Synthesis of esters and amides of 2-aryl-1-hydroxy-4-methyl-1H-imidazole-5-carboxylic acids and study of their antiviral activity against orthopoxviruses.Bioorg. Med. Chem. Lett.20237912908010.1016/j.bmcl.2022.129080 36414175
     [Google Scholar]
  11. AlluruS SailajaBBV PalA Synthesis, characterization and anticancer evaluation of new 1H-naphtho[2,3-d]imidazole-4,9-dione-1,2,4-oxadiazole hybrids.Chem Biol Lett2023101506-6
     [Google Scholar]
  12. AkyüzG. Synthesis of benzimidazole derivatives containing Schiff base exhibiting antiurease activities.Cumhur. Sci. J.202142364965510.17776/csj.867783
     [Google Scholar]
  13. AwasthiA. RahmanM.A. Bhagavan RajuM. Synthesis, in silico studies, and in vitro anti-inflammatory activity of novel imidazole derivatives targeting P38 MAP kinase.ACS Omega20238201778817799
     [Google Scholar]
  14. AttramH.D. KorkorC.M. TaylorD. NjorogeM. ChibaleK. Antimalarial imidazopyridines incorporating an intramolecular hydrogen bonding motif: Medicinal chemistry and mechanistic studies.ACS Infect. Dis.20239492894210.1021/acsinfecdis.2c00584 36946433
     [Google Scholar]
  15. MarzoukA.A. BassA.K.A. AhmedM.S. Design, synthesis and anticonvulsant activity of new imidazolidindione and imidazole derivatives.Bioorg. Chem.202010110402010.1016/j.bioorg.2020.104020 32599366
     [Google Scholar]
  16. RaghuM.S. Pradeep KumarC.B. Yogesh KumarK. Design, synthesis and molecular docking studies of imidazole and benzimidazole linked ethionamide derivatives as inhibitors of InhA and antituberculosis agents.Bioorg. Med. Chem. Lett.20226012860410.1016/j.bmcl.2022.128604 35123004
     [Google Scholar]
  17. HaghighijooZ. FiruziO. MeiliS. EdrakiN. KhoshneviszadehM. MiriR. Design and synthesis of novel 1-hydroxy-2,4,5-triaryl Imidazole derivatives as anti-cytokine agents.Iran. J. Pharm. Res.2020191181191 32922479
     [Google Scholar]
  18. RashamuseT.J. FishM.Q. CoyanisE.M. BodeM.L. Studies towards the design and synthesis of novel 1,5-Diaryl-1H-imidazole-4-carboxylic acids and 1,5-Diaryl-1H-imidazole-4-carbohydrazides as Host LEDGF/p75 and HIV-1 integrase interaction inhibitors.Molecules20212620620310.3390/molecules26206203 34684786
     [Google Scholar]
  19. AshrafZ. RafiqM. SeoS.Y. BabarM.M. ZaidiN.S.S. Design, synthesis and bioevaluation of novel umbelliferone analogues as potential mushroom tyrosinase inhibitors.J. Enzyme Inhib. Med. Chem.201530687488310.3109/14756366.2014.979346 25643758
     [Google Scholar]
  20. AbbasQ. AshrafZ. HassanM. Development of highly potent melanogenesis inhibitor by in vitro, in vivo and computational studies.Drug Des. Devel. Ther.2017112029204610.2147/DDDT.S137550 28740364
     [Google Scholar]
  21. AshrafZ. RafiqM. SeoS.Y. BabarM.M. ZaidiN.S.S. Synthesis, kinetic mechanism and docking studies of vanillin derivatives as inhibitors of mushroom tyrosinase.Bioorg. Med. Chem.201523175870588010.1016/j.bmc.2015.06.068 26204890
     [Google Scholar]
  22. AshrafZ. RafiqM. SeoS.Y. KwonK.S. BabarM.M. Sadaf ZaidiN-S. Kinetic and in silico studies of novel hydroxy-based thymol analogues as inhibitors of mushroom tyrosinase.Eur. J. Med. Chem.20159820321110.1016/j.ejmech.2015.05.031 26025140
     [Google Scholar]
  23. Al-RooqiM.M. SadiqA. ObaidR.J. Evaluation of 2,3-Dihydro-1,5-benzothiazepine derivatives as potential tyrosinase inhibitors: In vitro and in silico studies.ACS Omega2023819171951720810.1021/acsomega.3c01566 37214694
     [Google Scholar]
  24. NazirY. RafiqueH. KausarN. Methoxy-substituted tyramine derivatives synthesis, computational studies and tyrosinase inhibitory kinetics.Molecules2021269247710.3390/molecules26092477 33922836
     [Google Scholar]
  25. NazirY. SaeedA. RafiqM. Hydroxyl substituted benzoic acid/cinnamic acid derivatives: Tyrosinase inhibitory kinetics, anti-melanogenic activity and molecular docking studies.Bioorg. Med. Chem. Lett.202030112672210.1016/j.bmcl.2019.126722 31732410
     [Google Scholar]
  26. RafiqM. NazirY. AshrafZ. Synthesis, computational studies, tyrosinase inhibitory kinetics and antimelanogenic activity of hydroxy substituted 2-[(4-acetylphenyl)amino]-2-oxoethyl derivatives.J. Enzyme Inhib. Med. Chem.20193411562157210.1080/14756366.2019.1654468 31456445
     [Google Scholar]
/content/journals/cpd/10.2174/0113816128330769241113095033
Loading
One-pot, Four-component Synthesis, Molecular Docking and Pharmacokinetic Studies of Tetra-substituted Imidazole Derivatives as Potential Mushroom Tyrosinase Inhibitors
Curr. Pharm. Des. 31, 1078 (2025); https://doi.org/10.2174/0113816128330769241113095033
/content/journals/cpd/10.2174/0113816128330769241113095033
/content/journals/cpd/10.2174/0113816128330769241113095033
Loading

Data & Media loading...


  • Article Type:     Research Article
Keyword(s): aromatic aldehydes; biological activities; molecular docking; mushroom tyrosinase inhibitors; One-pot synthesis; pharmacokinetic studies

Most Cited Most Cited RSS feed

This is a required field
Please enter a valid email address
Approval was a Success
Invalid data
An Error Occurred
Approval was partially successful, following selected items could not be processed due to error
Please enter a valid_number test